of basel



Patented Oct. 9,1928.

UNITED srA TES - ERNST ROTH LIN AND FRITZ MULLEB, OF BASED, SWITZERLAND, ASSIGNOR 1'0 THE PATENT OFFICE.-

FIBM CHEMICAL WORKS FORI ERLi SANDOZ, OF BASEL, SWITZERLAND.

'nmn'rrnn DERIVATIVES ron 'rnanaraurrcan runrosns.

No Drawing. Application filed December 22,1927, Serial No. 242,607, in switzerland January 12, 1927.

It hasbeen found that new and valuable emetine salts as well as salts of other cephaeline alkvlethers can be obtained by coupling these alkaloids with bile acidsvtoform bile 5 acid salts. As bile acids glycocholic taurm cholic, cholic, desoxycholic, apochollc, de-

- hvdrocholi'c and choleinicacid may enter mto consideration. Y

The preparation of these new salts may easily be carried out, if these ac ds and the bases are allowed to interact in molecular.

proportions or by double decomposition of suitable salts of the original materials.

The new salts possess a stronger antiparasitic action than the known ones. They constitute in general slightly yellowish powders,"

easily soluble in alcohol and methanol, more. diflicultly soluble. in acetone and ether, nearly insoluble in water.

"The following examples illustrate the invention; I

Emample 1.5,5 g. of emetine and 4,3 g. of

cholic acid are combined in an alcoholic solution. As soon as the substances are dissolved the solvent is evaporated and the frothy residue dried in vacuo at elevated temperature.

' The, slightly yellowish chola'te of emetine is;

' easily soluble in alcohol,methanoland chloro- 'for more 'diflicultly in acetone and ether,

an nearly insoluble in water. It possesses a ple 1. The desoxycholate .of emetine, a

slightly yellowish powder, is worked up in an analogous manner and possesses the same solubility propertiesas emetine cholate.

Emample 4.--5,6- gof-cephaeline ethyl;

ether is allowed to interact with 4,3 g. of cholic acid. Thei cholate of cephaeline ethylether is a slightly yellowish powder, possessing the same solubility properties as emetine cholate.

What we claim is:

1. As new articles of manufacture, bile acid salts of cephaeline alkylethers, being slightly yellowish powders, easily soluble in alcohol and methanol, more diflicultlv soluble in acetone and ether, nearly insoluble in water and possessing a strong antiparasitic action.

- 2. As new articles oi manufacture, salts of saponified bile acids of cephaeline 'alkylethers,

being slightly yellowish powders, easily solublein alcohol and methanol, more diflicultly soluble in acetone and ether, nearly insoluble in water and possessing a strong antiparasitic" action.

3. As new articles of manufacture, salts of cholic acid of cephaeline alkylethers,being shghtly yellowish powders, "easily soluble in alcohol and methanol, more diflicultly soluble water and possessing'a strong antiparasitic in acetone and ether, nearly insoluble in action.

1. As a new article of manufacture, the cholate of emetine, constituting a slightly yellowish powder, easily soluble in' alcohol andmethanol, more-difiicultly soluble in acetoneand ether, nearly insoluble in water -andpossessing a strong antiparasitic action.

In witness whereof We have hereunto signed day of December, 1927. ERNST ROTHLIN. FRITZ MULLER.

our names this 12th 

